JP2020505395A5 - - Google Patents
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- Publication number
- JP2020505395A5 JP2020505395A5 JP2019540035A JP2019540035A JP2020505395A5 JP 2020505395 A5 JP2020505395 A5 JP 2020505395A5 JP 2019540035 A JP2019540035 A JP 2019540035A JP 2019540035 A JP2019540035 A JP 2019540035A JP 2020505395 A5 JP2020505395 A5 JP 2020505395A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- prodrug
- pharmaceutically acceptable
- acceptable salt
- stereoisomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000000651 prodrug Substances 0.000 claims description 34
- 229940002612 prodrugs Drugs 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000011780 sodium chloride Substances 0.000 claims description 34
- 102200124918 NRAS G12C Human genes 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 102100009283 HRAS Human genes 0.000 claims description 14
- 101710033925 HRAS Proteins 0.000 claims description 14
- 102100009279 KRAS Human genes 0.000 claims description 14
- 101710033922 KRAS Proteins 0.000 claims description 14
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 14
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 10
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 230000035772 mutation Effects 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- -1 heterocyclylene Chemical group 0.000 claims description 9
- 102200006538 KRAS G12C Human genes 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 102200006614 HRAS G12C Human genes 0.000 claims description 6
- 230000001404 mediated Effects 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 102000008300 Mutant Proteins Human genes 0.000 claims description 4
- 108010021466 Mutant Proteins Proteins 0.000 claims description 4
- 208000008443 Pancreatic Carcinoma Diseases 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 201000011231 colorectal cancer Diseases 0.000 claims description 4
- 201000005787 hematologic cancer Diseases 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 201000002528 pancreatic cancer Diseases 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 235000018102 proteins Nutrition 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 206010027476 Metastasis Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N Amino radical Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- JYZIHLWOWKMNNX-UHFFFAOYSA-N Benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N OBO Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000005418 aryl aryl group Chemical group 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 230000035755 proliferation Effects 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 230000000155 isotopic Effects 0.000 claims 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 206010056981 Adenomatous polyposis coli Diseases 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002830 nitrogen compounds Chemical class 0.000 claims 1
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- BDYKZMNDOYRQTR-UHFFFAOYSA-N CC(C)(C)c(c(F)ccc1)c1O Chemical compound CC(C)(C)c(c(F)ccc1)c1O BDYKZMNDOYRQTR-UHFFFAOYSA-N 0.000 description 3
- BQBGTRIOPZRLJD-UHFFFAOYSA-N CC(C)(C)c1cc(O)cc2c1cccc2 Chemical compound CC(C)(C)c1cc(O)cc2c1cccc2 BQBGTRIOPZRLJD-UHFFFAOYSA-N 0.000 description 3
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Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO3805B1 (ar) | 2013-10-10 | 2021-01-31 | Araxes Pharma Llc | مثبطات كراس جي12سي |
| CN108779097A (zh) | 2015-11-16 | 2018-11-09 | 亚瑞克西斯制药公司 | 包含取代的杂环基的2-取代的喹唑啉化合物及其使用方法 |
| WO2017172979A1 (en) | 2016-03-30 | 2017-10-05 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use |
| CA3024523A1 (en) | 2016-05-18 | 2017-11-23 | Mirati Therapeutics, Inc. | Kras g12c inhibitors |
| HUE056777T2 (hu) | 2016-12-22 | 2022-03-28 | Amgen Inc | Benzizotiazol-, izotiazolo[3,4-b]piridin-, kinazolin-, ftálazin-, pirido[2,3-d]piridazin- és pirido[2,3-d]pirimidin-származékok mint KRAS G12C inhibitorok tüdõ-, hasnyálmirigy- vagy vastagbélrák kezelésére |
| WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
| CN110382482A (zh) | 2017-01-26 | 2019-10-25 | 亚瑞克西斯制药公司 | 稠合的杂-杂二环化合物及其使用方法 |
| US11274093B2 (en) | 2017-01-26 | 2022-03-15 | Araxes Pharma Llc | Fused bicyclic benzoheteroaromatic compounds and methods of use thereof |
| US11136308B2 (en) | 2017-01-26 | 2021-10-05 | Araxes Pharma Llc | Substituted quinazoline and quinazolinone compounds and methods of use thereof |
| WO2018140513A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | 1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1yl)prop-2-en-1-one derivatives and similar compounds as kras g12c modulators for treating cancer |
| JOP20190272A1 (ar) | 2017-05-22 | 2019-11-21 | Amgen Inc | مثبطات kras g12c وطرق لاستخدامها |
| US10745385B2 (en) | 2017-05-25 | 2020-08-18 | Araxes Pharma Llc | Covalent inhibitors of KRAS |
| WO2018218069A1 (en) | 2017-05-25 | 2018-11-29 | Araxes Pharma Llc | Quinazoline derivatives as modulators of mutant kras, hras or nras |
| JP7150823B2 (ja) | 2017-09-08 | 2022-10-11 | アムジエン・インコーポレーテツド | ＫＲａｓ Ｇ１２Ｃの阻害剤及びそれを使用する方法 |
| HUE061599T2 (hu) | 2017-11-15 | 2023-07-28 | Mirati Therapeutics Inc | KRas G12C inhibotorok |
| US10647715B2 (en) | 2017-11-15 | 2020-05-12 | Mirati Therapeutics, Inc. | KRas G12C inhibitors |
| US11090304B2 (en) | 2018-05-04 | 2021-08-17 | Amgen Inc. | KRAS G12C inhibitors and methods of using the same |
| JP7361722B2 (ja) | 2018-05-04 | 2023-10-16 | アムジエン・インコーポレーテツド | Ｋｒａｓ ｇ１２ｃ阻害剤及び同一物の使用方法 |
| WO2019217307A1 (en) | 2018-05-07 | 2019-11-14 | Mirati Therapeutics, Inc. | Kras g12c inhibitors |
| TW202012415A (zh) | 2018-05-08 | 2020-04-01 | 瑞典商阿斯特捷利康公司 | 化學化合物 |
| EP3790886A1 (en) | 2018-05-10 | 2021-03-17 | Amgen Inc. | Kras g12c inhibitors for the treatment of cancer |
| WO2019232419A1 (en) | 2018-06-01 | 2019-12-05 | Amgen Inc. | Kras g12c inhibitors and methods of using the same |
| AU2019336588B2 (en) | 2018-06-12 | 2022-07-28 | Amgen Inc. | KRAS G12C inhibitors encompassing a piperazine ring and use thereof in the treatment of cancer |
| EP3628664A1 (en) * | 2018-09-25 | 2020-04-01 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Irreversible inhibitors of kras g12c mutant |
| JP2020090482A (ja) | 2018-11-16 | 2020-06-11 | アムジエン・インコーポレーテツド | Ｋｒａｓ ｇ１２ｃ阻害剤化合物の重要な中間体の改良合成法 |
| CA3117222A1 (en) * | 2018-11-19 | 2020-05-28 | Amgen Inc. | Kras g12c inhibitors and methods of using the same |
| JP7377679B2 (ja) | 2018-11-19 | 2023-11-10 | アムジエン・インコーポレーテツド | がん治療のためのｋｒａｓｇ１２ｃ阻害剤及び１種以上の薬学的に活性な追加の薬剤を含む併用療法 |
| EP3908283A4 (en) | 2019-01-10 | 2022-10-12 | Mirati Therapeutics, Inc. | KRAS G12C INHIBITORS |
| WO2020165732A1 (en) | 2019-02-12 | 2020-08-20 | Novartis Ag | Pharmaceutical combination comprising tno155 and a krasg12c inhibitor |
| EP3738593A1 (en) | 2019-05-14 | 2020-11-18 | Amgen, Inc | Dosing of kras inhibitor for treatment of cancers |
| SG11202112855WA (en) | 2019-05-21 | 2021-12-30 | Amgen Inc | Solid state forms |
| JP2022546043A (ja) | 2019-08-29 | 2022-11-02 | ミラティ セラピューティクス， インコーポレイテッド | Ｋｒａｓ ｇ１２ｄ阻害剤 |
| MX2022003537A (es) | 2019-09-24 | 2022-07-11 | Mirati Therapeutics Inc | Terapias de combinacion. |
| EP4051678A1 (en) | 2019-10-28 | 2022-09-07 | Merck Sharp & Dohme Corp. | Small molecule inhibitors of kras g12c mutant |
| MX2022005359A (es) | 2019-11-04 | 2022-06-02 | Revolution Medicines Inc | Inhibidores de ras. |
| EP4055028A1 (en) | 2019-11-04 | 2022-09-14 | Revolution Medicines, Inc. | Ras inhibitors |
| AU2020379731A1 (en) | 2019-11-04 | 2022-05-05 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2021108683A1 (en) | 2019-11-27 | 2021-06-03 | Revolution Medicines, Inc. | Covalent ras inhibitors and uses thereof |
| MX2022007515A (es) | 2019-12-20 | 2022-09-19 | Mirati Therapeutics Inc | Inhibidores de sos1. |
| WO2021120890A1 (en) | 2019-12-20 | 2021-06-24 | Novartis Ag | Pyrazolyl derivatives useful as anti-cancer agents |
| JP2023529867A (ja) | 2020-06-05 | 2023-07-12 | キネート バイオファーマ インク． | 線維芽細胞増殖因子受容体キナーゼの阻害剤 |
| AU2021293228A1 (en) | 2020-06-18 | 2023-02-09 | Revolution Medicines, Inc. | Methods for delaying, preventing, and treating acquired resistance to RAS inhibitors |
| AU2021344830A1 (en) | 2020-09-03 | 2023-04-06 | Revolution Medicines, Inc. | Use of SOS1 inhibitors to treat malignancies with SHP2 mutations |
| KR20230067635A (ko) | 2020-09-15 | 2023-05-16 | 레볼루션 메디슨즈, 인크. | 암의 치료에서 ras 억제제로서 인돌 유도체 |
| WO2022133345A1 (en) | 2020-12-18 | 2022-06-23 | Erasca, Inc. | Tricyclic pyridones and pyrimidones |
| US20240100172A1 (en) | 2020-12-21 | 2024-03-28 | Hangzhou Jijing Pharmaceutical Technology Limited | Methods and compounds for targeted autophagy |
| WO2022235864A1 (en) | 2021-05-05 | 2022-11-10 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2022235870A1 (en) | 2021-05-05 | 2022-11-10 | Revolution Medicines, Inc. | Ras inhibitors for the treatment of cancer |
| WO2022266206A1 (en) | 2021-06-16 | 2022-12-22 | Erasca, Inc. | Kras inhibitor conjugates |
| TW202317100A (zh) | 2021-06-23 | 2023-05-01 | 瑞士商諾華公司 | 包含ｋｒａｓ ｇ１２ｃ抑制劑的藥物組合及其用於治療癌症之用途 |
| WO2023031781A1 (en) | 2021-09-01 | 2023-03-09 | Novartis Ag | Pharmaceutical combinations comprising a tead inhibitor and uses thereof for the treatment of cancers |
| AR127308A1 (es) | 2021-10-08 | 2024-01-10 | Revolution Medicines Inc | Inhibidores ras |
| TW202333689A (zh) * | 2021-10-13 | 2023-09-01 | 美商雷密克斯醫療公司 | 調節剪接之化合物及方法 |
| WO2023114954A1 (en) | 2021-12-17 | 2023-06-22 | Genzyme Corporation | Pyrazolopyrazine compounds as shp2 inhibitors |
| EP4227307A1 (en) | 2022-02-11 | 2023-08-16 | Genzyme Corporation | Pyrazolopyrazine compounds as shp2 inhibitors |
| WO2023172940A1 (en) | 2022-03-08 | 2023-09-14 | Revolution Medicines, Inc. | Methods for treating immune refractory lung cancer |
| WO2023199180A1 (en) | 2022-04-11 | 2023-10-19 | Novartis Ag | Therapeutic uses of a krasg12c inhibitor |
| WO2023240263A1 (en) | 2022-06-10 | 2023-12-14 | Revolution Medicines, Inc. | Macrocyclic ras inhibitors |
| WO2024102421A2 (en) | 2022-11-09 | 2024-05-16 | Revolution Medicines, Inc. | Compounds, complexes, and methods for their preparation and of their use |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6143190A (ja) * | 1984-08-06 | 1986-03-01 | Mitsui Petrochem Ind Ltd | ピリドピリミジン誘導体およびその製法 |
| US5033252A (en) | 1987-12-23 | 1991-07-23 | Entravision, Inc. | Method of packaging and sterilizing a pharmaceutical product |
| US5052558A (en) | 1987-12-23 | 1991-10-01 | Entravision, Inc. | Packaged pharmaceutical product |
| GB8827305D0 (en) | 1988-11-23 | 1988-12-29 | British Bio Technology | Compounds |
| US5323907A (en) | 1992-06-23 | 1994-06-28 | Multi-Comp, Inc. | Child resistant package assembly for dispensing pharmaceutical medications |
| US5455258A (en) | 1993-01-06 | 1995-10-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
| US5863949A (en) | 1995-03-08 | 1999-01-26 | Pfizer Inc | Arylsulfonylamino hydroxamic acid derivatives |
| WO1996033172A1 (en) | 1995-04-20 | 1996-10-24 | Pfizer Inc. | Arylsulfonyl hydroxamic acid derivatives as mmp and tnf inhibitors |
| EP0780386B1 (en) | 1995-12-20 | 2002-10-02 | F. Hoffmann-La Roche Ag | Matrix metalloprotease inhibitors |
| EP0923585B1 (en) | 1996-07-18 | 2002-05-08 | Pfizer Inc. | Phosphinate based inhibitors of matrix metalloproteases |
| SK21499A3 (en) | 1996-08-23 | 2000-05-16 | Pfizer | Arylsulfonylamino hydroxamic acid derivatives |
| BR9714266A (pt) | 1997-01-06 | 2000-04-18 | Pfizer | Derivados de sulfona cìclicos. |
| PL335027A1 (en) | 1997-02-03 | 2000-03-27 | Pfizer Prod Inc | Derivatives of arylsulphonylamino hydroxamic acid |
| AU5493598A (en) | 1997-02-07 | 1998-08-26 | Pfizer Inc. | N-hydroxy-beta-sulfonyl-propionamide derivatives and their use as inhibitors of matrix metalloproteinases |
| AU722784B2 (en) | 1997-02-11 | 2000-08-10 | Pfizer Inc. | Arylsulfonyl hydroxamic acid derivatives |
| GB9725782D0 (en) | 1997-12-05 | 1998-02-04 | Pfizer Ltd | Therapeutic agents |
| GB9801690D0 (en) | 1998-01-27 | 1998-03-25 | Pfizer Ltd | Therapeutic agents |
| PA8469501A1 (es) | 1998-04-10 | 2000-09-29 | Pfizer Prod Inc | Hidroxamidas del acido (4-arilsulfonilamino)-tetrahidropiran-4-carboxilico |
| PA8469401A1 (es) | 1998-04-10 | 2000-05-24 | Pfizer Prod Inc | Derivados biciclicos del acido hidroxamico |
| JP2004250329A (ja) * | 2002-12-26 | 2004-09-09 | Dainippon Pharmaceut Co Ltd | イサチン誘導体 |
| GB0405628D0 (en) * | 2004-03-12 | 2004-04-21 | Glaxo Group Ltd | Novel compounds |
| KR101256018B1 (ko) * | 2009-08-20 | 2013-04-18 | 한국과학기술연구원 | 단백질 키나아제 저해활성을 갖는 1,3,6-치환된 인돌 화합물 |
| MX355943B (es) * | 2013-06-26 | 2018-05-07 | Abbvie Inc | Carboxamidas primarias como inhibidores de btk. |
| MX369863B (es) * | 2013-08-23 | 2019-11-25 | Neupharma Inc | Ciertas entidades quimicas, composiciones y metodos. |
| JO3805B1 (ar) * | 2013-10-10 | 2021-01-31 | Araxes Pharma Llc | مثبطات كراس جي12سي |
| CN106488910B (zh) * | 2013-10-10 | 2020-07-31 | 亚瑞克西斯制药公司 | Kras g12c的抑制剂 |
| EP3277678B1 (en) * | 2015-04-03 | 2020-03-18 | NantBio, Inc. | Compositions and methods of targeting mutant k-ras |
| CN105399734A (zh) * | 2015-12-23 | 2016-03-16 | 吉林省长源药业有限公司 | 新型egfr抑制剂及其制备方法 |
| CN105348271A (zh) * | 2015-12-23 | 2016-02-24 | 常州润诺生物科技有限公司 | 喹唑啉类衍生物药用用途及其制备方法 |
| CN105924840A (zh) * | 2016-06-01 | 2016-09-07 | 扬州兰都塑料科技有限公司 | 一种阻燃电力电缆 |
| CN106084164A (zh) * | 2016-06-12 | 2016-11-09 | 四川大学 | 一种结构抗菌型聚氨酯用扩链剂的制备方法 |
-
2018
- 2018-01-25 US US16/480,849 patent/US20200385364A1/en not_active Abandoned
- 2018-01-25 EP EP18704371.6A patent/EP3573966A1/en not_active Withdrawn
- 2018-01-25 CN CN201880008592.8A patent/CN110382483A/zh active Pending
- 2018-01-25 JP JP2019540035A patent/JP2020505395A/ja active Pending
- 2018-01-25 WO PCT/US2018/015227 patent/WO2018140598A1/en unknown
-
2022
- 2022-06-13 US US17/839,232 patent/US20230147053A1/en active Pending
-
2023
- 2023-01-23 JP JP2023008128A patent/JP2023041763A/ja active Pending
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